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Bromination of aromatics using hexabromoacetone |
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| รหัสดีโอไอ | |
| Title | Bromination of aromatics using hexabromoacetone |
| Creator | Nat Tohsamrit |
| Contributor | Warinthorn Chavasiri |
| Publisher | Chulalongkorn University |
| Publication Year | 2557 |
| Keyword | โบรมิเนชัน, สารประกอบอะโรมาติก, Bromination, Aromatic compounds |
| Abstract | A novel, mild and high yielding synthetic method for the bromination of aromatics using hexabromoacetone (HBA) is disclosed. Using anisole as a template, various parameters including UV radiation, temperature, time, the substrate concentration, molar ratio of anisole: HBA and additives were explored to search for optimum conditions which led to the selective production of the corresponding 4-bromoanisole in high yield in short reaction time. Twelve aromatics were examined and found that aromatics with electron-donating group were very reactive forming di- or tri-substituted products. The regioselectivity of the reaction could be controlled by using different ratios of substrate to HBA, solvent, reaction time, or adding HBA in small portion. Several chemical probes including allylbenzene, safrole, 4′-chloroflavanone, flavone and pinostrobin were selected to investigate the scope of this reaction. The trend of the reactivity could be observed in order for the bromination towards unsaturated portion > aromatic with activating group > α-carbonyl group. The reaction pathway was believed to occur via Br2 generated in situ from HBA. |
| URL Website | cuir.car.chula.ac.th |
